Azodyestuffs insoluble in water and process of making same



?aterrted Feb. 23, 1932 UNITED STATES PATENT OFFICE ARTHUR ZITSCHER, OF OFFENBACH-ON-TI-IE-MAIN, AND ROBERT vSGHIMIELT, .OF DARMSTADT, GERMANY, ASSIGNORS TO GENERAL ANILINE WORKS 11vo.,;or;nnw YORK, N. Y., l-l. CORPORATION OF DELAWARE AZODYESTUFFSINSOLUBLE IN WATER AND PROCESS. OF MAKING SAME No Drawing. Application filed April 3, 1929, Serial No. 352,319, and in Gcrmany April 7,1928.

The present invention relates to azo dyestutls insoluble in Water and to a process of preparing the same.

We have found that valuable azo dyestuifs 5 insoluble in Water are obtained by combining any diazo-, tetrazoor diazoazo-compound not containing sulfonic or carboxylic groups with a dihydroxy-quinoline-compound of the probable general formula fast dyeings and printings on the fiber by.

producing the dyestuffs according to the icecolor method. In consequence of the substantive properties of these combining components the goods padded therewith may be developed without being previously dried.

In order to further illustrate our invention the following examples are given, the parts being by weight and all temperatures in centigrade degrees, but it may be understood that our invention is not limited to the particular products or conditions of reaction mentioned therein.

Ezrample 1 Cotton yarn previously treated in a suit able manner is padded with a solution containing per litre 4 grs. of 1 (QeV-dihydroxy- 6quinolyl)-2.3-pheno-triazole of the probable formula (nearly colorless needles melting above 330, prepared from 1-(4-amino-3-carbethoxyphenyl) -2.3-pheno-triazole and malonic ester in an analogous manner as described inu Bier. d. Deutsch. Chem. Ges, vol. 60, page 1108),

Hi HO-(B 8 com. of a caustic soda solution of 3 1 Be,

8 com. of Turkey red oil and QSgrs. of Glaubers salt. Then it is wrung outand developed in the presence of acetic acid with a solution containing per liter a. hundredth molecular proportion of diazotized 3-amino- 4c.6-dichloro-l-methyl benzene. i

In this manner a reddish-yellow dyeing o a very good fastness is obtained. The following table shows theshades of dyeings pre pared in like manner from the same padding solution and from the diazo-compounds of the following bases i Base Shade g-ch1oro-2-amin0'aniso1e. 9-11itroQ-amindtolucnc. iam no-anthraquinone. oammo-azdtoluene.

5nitro-2-aznino anisolc.

Ycllowish-orangc. Reddish-yellow.

Deep reddish-yellow. Brownish red-orange. Brownish yellow-orange.

E azmnple 2 Cotton yarn previously treated in a suitable manner is padded. with a solution containing per liter 8 grs. of QA-dihydroxyquinoline-(S.1-azo-2-chloro-benzene of the probable formula on i l l a t N 1 or (orange-yellow powder melting above 345, prepared from 4- amino 2 -chloroo-azo-benzene-3-carboxylic acid and malonicester in The following table shows the shades of dyeings prepared in like manner from the same padding solution and from the diazocompounds of the following bases:

Base Shade 2.5-dich1oro-ani1ine. Furo yellow. 6-ch1oro-2-amino-t01uene. Pure yellow.

Golden-yellow. 4-ch1oro-2-amino'aniso1e Golden-orange.

We wish it to be understood that in the following claims the term combining means everywhere combining in substance or on a substratum especially on the vegetable fiber and that the term diazotized compound comprises diazo aswell as tetrazoand diazo-azo-compounds.

We claim 1. A rocess which comprises combining a diazotized compound not containing sulfonicor carboxyhc groups with a dihydroxy- I quinoline-compound of the probable formula: V

wherein R means a residue of the benzene series containing a radical of the group azo, azoxy, thiazole, imidazole, urea or triazole.

2. A process which comprises combining a diazotized compound not containing sulfonic or carboxylic groups with (24'-di-' hydroxy 6 quinolyl) 2.3 pheno triazole 0f the probable formula HIE/G l d 3. As new compounds the azo dyestuffs of the probable general formula:

,. wherein R means a residue of the benzene serles contaming a radical of the group azo,

azoxy, thiazole, imidazole, urea or triazole, which compounds are colored powders, insoluble in water, yielding valuable color lakes or when produced on the fiber fast dyeings and printings.

4. As new compounds the azo dyestuffs of the general probable formula:

wherein the aryl-group may contain further azo-groups, which compounds are colored powders, insoluble in water, yielding val;

uable color lakes or when produced on the fiber fast dyeings and printings.

In testimony whereof, I afiix my signature.

' ARTHUR ZITSOHER.

In testimony whereof, I aflix my signature.

- ROBERTv SCHMITT. 

